JP2008527154A5 - - Google Patents
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- JP2008527154A5 JP2008527154A5 JP2007551579A JP2007551579A JP2008527154A5 JP 2008527154 A5 JP2008527154 A5 JP 2008527154A5 JP 2007551579 A JP2007551579 A JP 2007551579A JP 2007551579 A JP2007551579 A JP 2007551579A JP 2008527154 A5 JP2008527154 A5 JP 2008527154A5
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- 239000000203 mixture Substances 0.000 claims description 31
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 150000003626 triacylglycerols Chemical class 0.000 claims description 15
- 239000002551 biofuel Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 239000000446 fuel Substances 0.000 claims description 5
- 125000005456 glyceride group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive Effects 0.000 claims description 3
- 238000007792 addition Methods 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- BVDRUCCQKHGCRX-UHFFFAOYSA-N 2,3-dihydroxypropyl formate Chemical compound OCC(O)COC=O BVDRUCCQKHGCRX-UHFFFAOYSA-N 0.000 description 5
- 229940088598 Enzyme Drugs 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 5
- 239000004367 Lipase Substances 0.000 description 5
- 238000006136 alcoholysis reaction Methods 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- 102000004882 lipase Human genes 0.000 description 5
- 108090001060 lipase Proteins 0.000 description 5
- DPUOLQHDNGRHBS-KTKRTIGZSA-N Erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 4
- 229940040461 Lipase Drugs 0.000 description 4
- 235000019484 Rapeseed oil Nutrition 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DTOSIQBPPRVQHS-PDBXOOCHSA-N α-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- ZVRMGCSSSYZGSM-CCEZHUSRSA-N (E)-hexadec-2-enoic acid Chemical compound CCCCCCCCCCCCC\C=C\C(O)=O ZVRMGCSSSYZGSM-CCEZHUSRSA-N 0.000 description 2
- 241000221089 Jatropha Species 0.000 description 2
- 229960004488 Linolenic Acid Drugs 0.000 description 2
- 241001661345 Moesziomyces antarcticus Species 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 241000223257 Thermomyces Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 description 2
- 229940108623 eicosenoic acid Drugs 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- BITHHVVYSMSWAG-KTKRTIGZSA-N gondoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 2
- 230000002209 hydrophobic Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 239000010496 thistle oil Substances 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000146387 Chromobacterium viscosum Species 0.000 description 1
- 241000222175 Diutina rugosa Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241000498617 Mucor javanicus Species 0.000 description 1
- 210000000496 Pancreas Anatomy 0.000 description 1
- 244000271379 Penicillium camembertii Species 0.000 description 1
- 235000002245 Penicillium camembertii Nutrition 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000235403 Rhizomucor miehei Species 0.000 description 1
- 241000588264 Rhizopus javanicus Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N Ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- WBHHMMIMDMUBKC-GKUQOKNUSA-N Ricinoleic acid Natural products CCCCCC[C@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-GKUQOKNUSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating Effects 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
菜種油は、通常、約４８重量％のエルカ酸、１５重量％のオレイン酸、１４重量％のリノール酸、８重量％のリノレン酸、５重量％のエイコセン酸、３重量％のパルミチン酸、２重量％のヘキサデセン酸および１重量％のドコサジエン酸を、脂肪酸成分として含有する。新しい植物からの菜種油は、より高水準の不飽和酸を有する。ここで、通常の脂肪酸水準は、エルカ酸０．５重量％、オレイン酸６３重量％、リノール酸２０重量％、リノレン酸９重量％、エイコセン酸１重量％、パルミチン酸４重量％、ヘキサデセン酸２重量％およびドコサジエン酸１重量％である。 Rapeseed oil is usually about 48% erucic acid, 15% oleic acid, 14% linoleic acid, 8% linolenic acid, 5% eicosenoic acid, 3% palmitic acid, 2% % Hexadecenoic acid and 1% by weight docosadienoic acid are included as fatty acid components. Rapeseed oil from new plants have higher levels of unsaturated acids. Here, the usual fatty acid levels are 0.5% by weight of erucic acid, 63% by weight of oleic acid, 20% by weight of linoleic acid, 9% by weight of linolenic acid, 1% by weight of eicosenoic acid, 4% by weight of palmitic acid, and 2 of hexadecenoic acid. % By weight and 1% by weight of docosadienoic acid.
ヒマシ油の８０〜８５重量％は、リシノール酸のグリセリドからなる。ヒマシ油はまた、約７重量％のオレイン酸グリセリド、３重量％のリノール酸グリセリドおよび約２重量％のパルミチン酸とステアリン酸のグリセリドを含有する。 80-85% by weight of castor oil consists of glycerides of ricinoleic acid. Castor oil also contains about 7 weight% of glycerides of oleic acid, 3% by weight of linoleic acid glycerides and about 2 wt% of palmitic acid and glycerides of stearic acid.
少量のエステラーゼ、好ましくはリパーゼの使用を通じて、非常に経済的に反応を行うことができる。反応は、酵素を強力に活性化させる添加アルカリ無機塩の存在下、酵素濃縮物によって直接行う。このような方法で、少量の酵素によって、固定化による酵素の安定化なしでさえ、高転化率が達成される。溶媒の添加は必要がない。 The reaction can be carried out very economically through the use of small amounts of esterases, preferably lipases. The reaction is carried out directly with the enzyme concentrate in the presence of added alkaline inorganic salts that strongly activate the enzyme. In this way, high conversion rates are achieved with a small amount of enzyme, even without stabilization of the enzyme by immobilization. It is not necessary to add a solvent.
説明：
セーボルト協会：独立して測定価値を決定するためのロッテルダムの協会
炭素残留マイクロ（１０％残留炭素分）：この試験は、ディーゼル中の炭素残渣を決定するために行われる。この目的で、試料を窒素流中で蒸発させ、残渣を秤量する。「マイクロ」は方法を表す。０．１％未満の残渣を生じさせようとする材料について、１０％蒸留残渣をまず調製し、次いで測定する。
蒸留挙動の決定：
ＩＢＰ：初期沸点
ＦＢＰ：最終沸点。百分率の数字は、それぞれの温度で蒸発させたディーゼルのパーセントを表す。
改善された潤滑性は、際立って有利であることとして明白である。
Explanation:
Saebold Association: Rotterdam Association for Independent Determination of Measurement Value Carbon Residual Micro (10% Residual Carbon Content): This test is performed to determine the carbon residue in diesel. For this purpose, the sample is evaporated in a stream of nitrogen and the residue is weighed. “Micro” represents a method. For materials that are intended to produce less than 0.1% residue, a 10% distillation residue is first prepared and then measured.
Determination of distillation behavior:
IBP: Initial boiling point FBP: Final boiling point. The percentage numbers represent the percentage of diesel evaporated at each temperature.
The improved lubricity is evident as a significant advantage.
結果：
化学的な部分エステル化によって、エステルと部分グリセリドからなる生成混合物が得られ、そこから大部分のグリセロールを洗浄のみによって容易に除去し得る。得られた混合物は単一相混合物である。トリグリセリド中に存在する１０％グリセロールの全てのうち、５０％未満が部分エステル交換において放出される。残りのグリセロールは、生成物中で結合したままである。よって、副生成物グリセロール流が半分以上、このプロセス中で低減される。
本明細書の当初の開示は、少なくとも下記の態様を包含する。
〔１〕ａ）炭素数１〜８のアルキル基を有するアルキルエステルと、ｂ）部分グリセリド、を含有し、組成物の総量に基づき、最大２重量％の遊離グリセロール含量を有することを特徴とする組成物。
〔２〕メチルおよび／またはエチルエステルを成分（ａ）として含有することを特徴とする、〔１〕に記載の組成物。
〔３〕組成物の総量に基づき、少なくとも１０重量％の部分グリセリド含量を有することを特徴とする、〔１〕〜〔２〕のいずれかに記載の組成物。
〔４〕組成物の総量に基づき、最大５重量％のトリグリセリド含量を有することを特徴とする、〔１〕〜〔３〕のいずれかに記載の組成物。
〔５〕最大５の酸価を有することを特徴とする、〔１〕〜〔４〕のいずれかに記載の組成物。
〔６〕アルキルエステル、モノグリセリドおよびジグリセリドが下記の量：
アルキルエステル：３０〜７０重量％
モノグリセリド：１０〜３５重量％
ジグリセリド：１〜３０重量％
で存在することを特徴とする、〔１〕〜〔５〕のいずれかに記載の組成物。
〔７〕アルキルエステルと部分グリセリドは、炭素数８〜２２の飽和または不飽和で直鎖状または分枝状の脂肪酸に由来することを特徴とする、〔１〕〜〔６〕のいずれかに記載の組成物。
〔８〕トリグリセリドをアルカリ塩の添加により活性化されたエステラーゼと酵素的に反応させ、該反応をアルコールの存在下に行うことを特徴とする、バイオ燃料の製造方法。
〔９〕エステラーゼを別の工程で失活させることを特徴とする、〔８〕に記載の方法。
〔１０〕１０℃〜４０℃の温度およびトリグリセリド量に基づき０．１〜１０重量％の含水量でアルコール分解を行うことを特徴とする、〔８〕〜〔９〕のいずれかに記載の方法。
〔１１〕市販の液体調製物のエステラーゼを、使用するトリグリセリド量に基づき、０．０５〜２％の量で使用することを特徴とする、〔８〕〜〔１０〕のいずれかに記載の方法。
〔１２〕ナトリウム、カリウム、カルシウム、マグネシウムおよびアンモニウムの水酸化物、炭酸塩およびリン酸塩からなる群から選択されるアルカリ無機塩の水溶液を、エステラーゼを活性化するために使用することを特徴とする、〔８〕〜〔１１〕のいずれかに記載の方法。
〔１３〕トリグリセリドに基づき、０．００００１〜１重量％の量で塩を使用することを特徴とする、〔１２〕に記載の方法。
〔１４〕トリグリセリドを、炭素数１〜８のアルコールの存在下で固定化および／または化学修飾されたエステラーゼと酵素的に反応させることを特徴とする、バイオ燃料の製造方法。
〔１５〕エステラーゼを生成混合物から別の工程で分離することを特徴とする、〔１４〕に記載の方法。
〔１６〕１０℃〜６０℃の温度およびトリグリセリド量に基づき０〜１０重量％の含水量でアルコール分解を行うことを特徴とする、〔１５〕〜〔１６〕のいずれかに記載の方法。
〔１７〕プラスチック、樹脂または鉱物基材上での疎水性相互作用により、もしくは、アニオンまたはカチオン交換体上でのイオン相互作用により、もしくは、活性化された化学基を有する基材への化学結合により、エステラーゼを固定化することを特徴とする、〔１４〕〜〔１６〕のいずれかに記載の方法。
〔１８〕界面活性剤で被覆することにより、酵素表面を疎水性化することにより、もしくは、 化学架橋することにより、エステラーゼを化学修飾することを特徴とする、〔１４〕〜〔１７〕のいずれかに記載の方法。
〔１９〕エステラーゼは、Ｔｈｅｒｍｏｍｙｃｅｓ ｌａｎｕｇｅｎｏｓｕｓ、Ｃａｎｄｉｄａ ａｎｔａｒｃｔｉｃａ Ａ、Ｃａｎｄｉｄａ ａｎｔａｒｃｔｉｃａ Ｂ、Ｒｈｉｚｏｍｕｃｏｒ ｍｉｅｈｅｉ、Ｃａｎｄｉｄａ ｃｙｌｉｎｄｒａｃｅａ、Ｒｈｉｚｏｐｕｓ ｊａｖａｎｉｃｕｓ、Ｐｏｒｃｉｎｅ ｐａｎｃｒｅａｓ、Ａｓｐｅｒｇｉｌｌｕｓ ｎｉｇｅｒ、Ｃａｎｄｉｄａ ｒｕｇｏｓａ、Ｍｕｃｏｒ ｊａｖａｎｉｃｕｓ、Ｐｓｅｕｄｏｍｏｎａｓ ｆｌｕｏｒｅｓｃｅｎｓ、Ｒｈｉｚｏｐｕｓ ｏｒｙｚａｅ、Ｐｓｅｕｄｏｍｐｎａｓ ｓｐ．、Ｃｈｒｏｍｏｂａｃｔｅｒｉｕｍ ｖｉｓｃｏｓｕｍ、Ｆｕｓａｒｉｕｍ ｏｘｙｓｐｏｒｕｍおよびＰｅｎｉｃｉｌｉｕｍ ｃａｍｅｍｂｅｒｔｉからなる群から選択される生物に由来することを特徴とする、〔８〕〜〔１３〕または〔１４〕〜〔１８〕のいずれかに記載の方法。
〔２０〕使用するエステラーゼはリパーゼであることを特徴とする、〔１９〕に記載の方法。
〔２１〕１，３−特異的リパーゼを使用することを特徴とする、〔１９〕〜〔２０〕のいずれかに記載の方法。
〔２２〕リパーゼは、Ｔｈｅｒｍｏｍｙｃｅｓ ｌａｎｕｇｅｎｏｓｕｓ由来のリパーゼであることを特徴とする、〔１９〕〜〔２１〕のいずれかに記載の方法。
〔２３〕高含有量百分率の一価および／または多価不飽和脂肪酸を有する油脂由来のトリグリセリドを使用することを特徴とする、〔８〕〜〔１３〕または〔１４〕〜〔１８〕および／または〔１９〕〜〔２２〕のいずれかに記載の方法。
〔２４〕ひまわり油，菜種油、アザミ油、大豆油、アマニ油、ピーナッツ油、獣脂、オリーブ油、ヒマシ油、パーム油、ヤトロファ油、パーム核油、ヤシ油およびオールドオイルからなる群から選択されるトリグリセリドを使用することを特徴とする、〔２３〕に記載の方法。
〔２５〕メタノールまたはエタノールをアルコール成分として使用することを特徴とする、〔８〕〜〔１３〕または〔１４〕〜〔１８〕および／または〔１９〕〜〔２２〕の少なくとも１項に記載の方法。
〔２６〕トリグリセリドに基づき、１０〜５０重量％の量でアルコールを使用することを特徴とする、〔８〕〜〔１３〕または〔１４〕〜〔１８〕および／または〔１９〕〜〔２２〕の少なくとも１項に記載の方法。
〔２７〕アルコールおよび／または水を部分的または完全に除去することを特徴とする、〔８〕〜〔１３〕または〔１４〕〜〔１８〕および／または〔１９〕〜〔２２〕の少なくとも１項に記載の方法。
〔２８〕炭素数１〜８のアルコールの存在下でトリグリセリドを部分的に化学反応させることを特徴とする、バイオ燃料の製造方法。
〔２９〕触媒を生成混合物から別の工程で分離することを特徴とする、〔２８〕に記載の方法。
〔３０〕使用した油に基づき１０モル％〜３０モル％のアルコール濃度でアルコール分解を行うことを特徴とする、〔２８〕〜〔２９〕のいずれかに記載の方法。
〔３１〕アルコール分解をエタノールまたはメタノールによって好適に行うことを特徴とする、〔２８〕〜〔３０〕のいずれかに記載の方法。
〔３２〕回分反応または連続反応として、並流または向流で、アルコール分解を行うことを特徴とする、〔２８〕〜〔３１〕のいずれかに記載の方法。
〔３３〕０．０１重量％〜５重量％の濃度で、２ｂａｒまでの圧力下、４０℃〜１２０℃の温度で、アルカリ金属アルコラートによってアルコール分解を行うことを特徴とする、〔２８〕〜〔３２〕のいずれかに記載の方法。
〔３４〕０．０１重量％〜５重量％の濃度で、５ｂａｒまでの圧力下、４０℃〜１２０℃の温度で、硫酸またはスルホン酸によってアルコール分解を行うことを特徴とする、〔２８〕〜〔３２〕のいずれかに記載の方法。
〔３５〕０．０１重量％〜１重量％の濃度で、２０〜２００ｂａｒの圧力下、１２０℃〜２５０℃の温度で、金属塩または金属石鹸によってアルコール分解を行うことを特徴とする、〔２８〕〜〔３２〕のいずれかに記載の方法。
〔３６〕高含有量百分率の一価および／または多価不飽和脂肪酸を有し、かつ、ひまわり油、菜種油、アザミ油、大豆油、アマニ油、ピーナッツ油，獣脂、オリーブ油、ヒマシ油、パーム油、ヤトロファ油、ヤシ油、パーム核油およびオールドオイルからなる群から選択される、油脂由来のトリグリセリドを使用することを特徴とする、〔２８〕〜〔３５〕のいずれかに記載の方法。
〔３７〕アルコールおよび／またはグリセロールおよび／または水を部分的または完全に除去することを特徴とする、〔２８〕〜〔３６〕のいずれかに記載の方法。
〔３８〕〔８〕〜〔３７〕のいずれかに記載の方法によって得ることのできる組成物。
〔３９〕９０〜９９．５重量％のガス油および０．５〜１０重量％（好ましくは２〜６重量％）の〔１〕〜〔７〕または〔３８〕に記載の組成物を添加剤として含有する燃料組成物。
〔４０〕〔１〕〜〔７〕または〔３８〕に記載の組成物の、バイオ燃料としての使用。
〔４１〕〔１〕〜〔７〕または〔３８〕に記載の組成物の、燃料組成物における添加剤としての使用。
〔４２〕〔１〕〜〔７〕または〔３８〕に記載の組成物の、燃料組成物の潤滑性能を向上させるための添加剤としての使用。
〔４３〕〔１〕〜〔７〕または〔３８〕に記載の組成物を０．５〜１０重量％の量で存在させることを特徴とする、〔４１〕または〔４２〕に記載の使用。
result:
Chemical partial esterification yields a product mixture consisting of esters and partial glycerides from which most of the glycerol can be easily removed by washing alone. The resulting mixture is a single phase mixture. Of all 10% glycerol present in the triglycerides, less than 50% is released in the partial transesterification. The remaining glycerol remains bound in the product. Thus, the by-product glycerol stream is reduced by more than half during this process.
The initial disclosure herein includes at least the following embodiments.
[1] It contains an alkyl ester having an alkyl group having 1 to 8 carbon atoms and b) a partial glyceride, and has a free glycerol content of up to 2% by weight based on the total amount of the composition. Composition.
[2] The composition according to [1], comprising methyl and / or ethyl ester as component (a).
[3] The composition according to any one of [1] to [2], wherein the composition has a partial glyceride content of at least 10% by weight based on the total amount of the composition.
[4] The composition according to any one of [1] to [3], having a triglyceride content of 5% by weight at the maximum based on the total amount of the composition.
[5] The composition according to any one of [1] to [4], which has an acid value of 5 at maximum.
[6] The following amounts of alkyl ester, monoglyceride and diglyceride:
Alkyl ester: 30 to 70% by weight
Monoglyceride: 10 to 35% by weight
Diglyceride: 1-30% by weight
The composition according to any one of [1] to [5], wherein
[7] The alkyl ester and the partial glyceride are derived from a saturated or unsaturated, linear or branched fatty acid having 8 to 22 carbon atoms, according to any one of [1] to [6] The composition as described.
[8] A method for producing a biofuel, characterized in that triglyceride is enzymatically reacted with an esterase activated by addition of an alkali salt, and the reaction is carried out in the presence of an alcohol.
[9] The method according to [8], wherein the esterase is inactivated in another step.
[10] The method according to any one of [8] to [9], wherein the alcoholysis is performed at a water content of 0.1 to 10% by weight based on a temperature of 10 ° C to 40 ° C and an amount of triglyceride. .
[11] The method according to any one of [8] to [10], wherein the esterase of a commercially available liquid preparation is used in an amount of 0.05 to 2% based on the amount of triglyceride used. .
[12] A feature of using an aqueous solution of an alkali inorganic salt selected from the group consisting of hydroxides, carbonates and phosphates of sodium, potassium, calcium, magnesium and ammonium for activating esterase. The method according to any one of [8] to [11].
[13] The method according to [12], wherein the salt is used in an amount of 0.00001 to 1% by weight based on triglyceride.
[14] A method for producing a biofuel, characterized in that triglyceride is enzymatically reacted with an esterase immobilized and / or chemically modified in the presence of an alcohol having 1 to 8 carbon atoms.
[15] The method according to [14], wherein the esterase is separated from the product mixture in a separate step.
[16] The method according to any one of [15] to [16], wherein the alcoholysis is performed at a water content of 0 to 10% by weight based on a temperature of 10 ° C to 60 ° C and an amount of triglyceride.
[17] Chemical bonding to substrates having activated chemical groups by hydrophobic interactions on plastic, resin or mineral substrates, or by ionic interactions on anions or cation exchangers The method according to any one of [14] to [16], wherein the esterase is immobilized by
[18] Any one of [14] to [17], wherein the esterase is chemically modified by coating with a surfactant, making the surface of the enzyme hydrophobic, or by chemical crosslinking The method of crab.
[19] esterases, Thermomyces lanugenosus, Candida antarctica A, Candida antarctica B, Rhizomucor miehei, Candida cylindracea, Rhizopus javanicus, Porcine pancreas, Aspergillus niger, Candida rugosa, Mucor javanicus, Pseudomonas fluorescens, Rhizopus oryzae, Pseudompnas sp. The method according to any one of [8] to [13] or [14] to [18], wherein the method is derived from an organism selected from the group consisting of Chromobacterium viscosum, Fusarium oxysporum, and Penicillium camemberti.
[20] The method according to [19], wherein the esterase used is a lipase.
[21] The method according to any one of [19] to [20], wherein a 1,3-specific lipase is used.
[22] The method according to any one of [19] to [21], wherein the lipase is a lipase derived from Thermomyces langenesus.
[23] A triglyceride derived from fats and oils having a high content percentage of monovalent and / or polyunsaturated fatty acids, [8] to [13] or [14] to [18] and / or Or the method in any one of [19]-[22].
[24] Triglyceride selected from the group consisting of sunflower oil, rapeseed oil, thistle oil, soybean oil, linseed oil, peanut oil, tallow, olive oil, castor oil, palm oil, jatropha oil, palm kernel oil, coconut oil and old oil The method according to [23], wherein: is used.
[25] The use according to at least one of [8] to [13] or [14] to [18] and / or [19] to [22], wherein methanol or ethanol is used as an alcohol component. Method.
[26] The alcohol is used in an amount of 10 to 50% by weight based on triglyceride, [8] to [13] or [14] to [18] and / or [19] to [22] The method according to at least one of the above.
[27] At least one of [8] to [13] or [14] to [18] and / or [19] to [22], wherein alcohol and / or water is partially or completely removed The method according to item.
[28] A method for producing a biofuel, wherein triglyceride is partially chemically reacted in the presence of an alcohol having 1 to 8 carbon atoms.
[29] The method according to [28], wherein the catalyst is separated from the product mixture in a separate step.
[30] The method according to any one of [28] to [29], wherein the alcoholysis is performed at an alcohol concentration of 10 mol% to 30 mol% based on the oil used.
[31] The method according to any one of [28] to [30], wherein the alcoholysis is suitably performed with ethanol or methanol.
[32] The method according to any one of [28] to [31], wherein the alcoholysis is performed in a cocurrent or countercurrent as a batch reaction or a continuous reaction.
[33] The alcohol decomposition is performed with an alkali metal alcoholate at a concentration of 0.01 wt% to 5 wt% and a pressure of up to 2 bar at a temperature of 40 ° C. to 120 ° C. 32].
[34] The alcohol decomposition is carried out with sulfuric acid or sulfonic acid at a concentration of 0.01% by weight to 5% by weight and a pressure of up to 5 bar at a temperature of 40 ° C. to 120 ° C. [32] The method according to any one of [32].
[35] The alcohol decomposition is performed with a metal salt or a metal soap at a concentration of 0.01% by weight to 1% by weight at a temperature of 120 ° C. to 250 ° C. under a pressure of 20 to 200 bar. ] The method in any one of [32].
[36] High content percentage of monovalent and / or polyunsaturated fatty acids and sunflower oil, rapeseed oil, thistle oil, soybean oil, linseed oil, peanut oil, tallow, olive oil, castor oil, palm oil The method according to any one of [28] to [35], wherein triglycerides derived from fats and oils selected from the group consisting of oil, jatropha oil, coconut oil, palm kernel oil and old oil are used.
[37] The method according to any one of [28] to [36], wherein alcohol and / or glycerol and / or water are partially or completely removed.
[38] A composition obtainable by the method according to any one of [8] to [37].
[39] 90 to 99.5% by weight of gas oil and 0.5 to 10% by weight (preferably 2 to 6% by weight) of the composition according to [1] to [7] or [38] As a fuel composition.
[40] Use of the composition according to [1] to [7] or [38] as a biofuel.
[41] Use of the composition according to [1] to [7] or [38] as an additive in a fuel composition.
[42] Use of the composition according to [1] to [7] or [38] as an additive for improving the lubricating performance of the fuel composition.
[43] The use according to [41] or [42], wherein the composition according to [1] to [7] or [38] is present in an amount of 0.5 to 10% by weight.
Claims (6)
ｂ）部分グリセリド、
を含有し、組成物の総量に基づき、最大２重量％の遊離グリセロール含量を有することを特徴とする組成物。 a) an alkyl ester having an alkyl group having 1 to 8 carbon atoms;
b) partial glycerides,
And a free glycerol content of up to 2% by weight, based on the total amount of the composition.
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| PCT/EP2006/000121 WO2006077023A2 (en) | 2005-01-19 | 2006-01-10 | Compositions which can be used as biofuel |
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| JPH03187385A (en) | 1983-11-10 | 1991-08-15 | Meito Sangyo Kk | Production of monoglyceride |
| FR2577569B1 (en) * | 1985-02-15 | 1987-03-20 | Inst Francais Du Petrole | PROCESS FOR THE MANUFACTURE OF A COMPOSITION OF FATTY ACID ESTERS FOR USE AS FUEL SUBSTITUTING GASOLINE WITH HYDRATED ETHYL ALCOHOL AND COMPOSITION OF ESTERS THUS FORMED |
| DE3512497A1 (en) | 1985-04-06 | 1986-10-09 | Hüls AG, 4370 Marl | METHOD FOR THE PRODUCTION OF CARBONIC ACID ALKYL ESTERS, ESPECIALLY FATTY ACID ALKYL ESTERS, AND THE USE THEREOF AS A DIESEL FUEL |
| WO1990004033A1 (en) | 1988-10-04 | 1990-04-19 | Enzytech, Inc. | Production of monoglycerides by enzymatic transesterification |
| US5316927A (en) | 1988-10-04 | 1994-05-31 | Opta Food Ingredients, Inc. | Production of monoglycerides by enzymatic transesterification |
| US5935828A (en) | 1989-05-01 | 1999-08-10 | Opta Food Ingredients, Inc. | Enzymatic production of monoglycerides containing omega-3 unsaturated fatty acids |
| EP0407959A3 (en) | 1989-07-11 | 1992-01-02 | Lion Corporation | Process for producing polyol fatty acid monoesters |
| JPH03103499A (en) | 1989-09-14 | 1991-04-30 | Meito Sangyo Kk | Production of highly unsaturated fatty acid monoglyceride |
| JPH03108489A (en) * | 1989-09-22 | 1991-05-08 | Meito Sangyo Kk | Production of long-chain highly unsaturated fatty acid monoglyceride |
| US5116745A (en) | 1990-04-19 | 1992-05-26 | The Procter & Gamble Company | Process for preparing 2-acylglycerides or 1,2-diacyl diglycerides or 2,3-diacyl diglycerides |
| US5149642A (en) | 1990-04-20 | 1992-09-22 | The Procter & Gamble Company | Process for preparing 2-acylglycerides or 1,2 or 2,3-diacylglycerides |
| GB9315205D0 (en) | 1993-07-22 | 1993-09-08 | Exxon Chemical Patents Inc | Additives and fuel compositions |
| FR2748490B1 (en) * | 1996-05-07 | 1998-06-19 | Inst Francais Du Petrole | PROCESS FOR THE MANUFACTURE OF ETHYL ESTERS |
| US5968792A (en) | 1996-12-19 | 1999-10-19 | Henkel Corporation | Calcium activation of lipase enzyme in process of pressure splitting glycerides |
| AU8760898A (en) * | 1997-09-24 | 1999-04-12 | Enzymotec Ltd. | Surfactant-lipase complex immobilized on insoluble matrix |
| FR2772391B1 (en) | 1997-12-15 | 2001-07-20 | Toulousaine De Rech Et De Dev | PROCESS FOR THE ENZYMATIC ALCOOLYSIS OF OLEIC SUNFLOWER OIL, IN PARTICULAR FOR THE MANUFACTURE OF A SURFACTANT LUBRICATING COMPOSITION |
| WO2000063322A1 (en) | 1999-04-21 | 2000-10-26 | Pure Fuels Usa, Inc. | Fuel compositions |
| EP1088880A1 (en) | 1999-09-10 | 2001-04-04 | Fina Research S.A. | Fuel composition |
| JP4530311B2 (en) | 2000-07-13 | 2010-08-25 | 日本水産株式会社 | Method for producing glyceride using lipase |
| JP4854889B2 (en) * | 2001-09-21 | 2012-01-18 | 株式会社レボインターナショナル | Method for producing diesel fuel oil from waste cooking oil |
| FR2838433B1 (en) | 2002-04-11 | 2005-08-19 | Inst Francais Du Petrole | PROCESS FOR PRODUCING ALKYL ESTERS FROM VEGETABLE OR ANIMAL OIL AND ALIPHATIC MONOALCOOL |
| JP4123899B2 (en) * | 2002-11-01 | 2008-07-23 | トヨタ自動車株式会社 | Fuel production method |
| ITMI20022627A1 (en) | 2002-12-12 | 2004-06-13 | Polimeri Europa Spa | USE OF A MIXTURE OF FATTY ACID ESTERS AS A FUEL |
| FR2852602B1 (en) * | 2003-03-17 | 2007-08-10 | Inst Francais Du Petrole | PROCESS FOR ALCOHOLICIZING VEGETABLE OR ANIMAL ACID OILS |
| JP4122433B2 (en) | 2003-08-18 | 2008-07-23 | 独立行政法人農業・食品産業技術総合研究機構 | Catalyst-free production method of biodiesel fuel that does not produce by-products |
-
2005
- 2005-01-19 DE DE102005002700A patent/DE102005002700A1/en not_active Withdrawn
-
2006
- 2006-01-10 JP JP2007551579A patent/JP5094413B2/en not_active Expired - Fee Related
- 2006-01-10 MX MX2007008658A patent/MX2007008658A/en active IP Right Grant
- 2006-01-10 BR BRPI0606422-1A patent/BRPI0606422A2/en not_active IP Right Cessation
- 2006-01-10 CA CA002595007A patent/CA2595007A1/en not_active Abandoned
- 2006-01-10 WO PCT/EP2006/000121 patent/WO2006077023A2/en active Application Filing
- 2006-01-10 EP EP06700480A patent/EP1838822A2/en not_active Withdrawn
- 2006-01-10 US US11/795,667 patent/US7799544B2/en not_active Expired - Fee Related
- 2006-01-10 CN CN2006800026880A patent/CN101479372B/en not_active Expired - Fee Related
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